1-立方烷甲酰胺 | 119696-06-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 1-立方烷甲酰胺
• 英文名称: cubanecarboxamide
• 英文别名: 1-cubanecarboxamide；Cubane-1-carboxamide
• CAS: 119696-06-9
• 化学式: C₉H₉NO
• mdl: MFCD19204366
• 分子量: 147.177
• InChiKey: HOEPPTNNJKHFJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-立方烷甲酰胺 在 吡啶 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 生成 cubanecarbonitrile
  参考文献：
  名称：

  Della, Ernest W.; Gangodawila, Hemakanthi, Australian Journal of Chemistry, 1989, vol. 42, # 9, p. 1485 - 1492

  摘要：

  DOI：
• 作为产物：
  描述：

  1-立方烷羧酸 在 草酰氯 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 1-立方烷甲酰胺
  参考文献：
  名称：

  4-取代的古柏碳烯基胺：一类新的基于机理的单胺氧化酶B灭活剂。

  摘要：

  合成了苄基羰基胺（1a），（4-环丙基cubyl）羰基胺（1b）和（4-苯基cubyl）羰基胺（1c），它们是时间依赖性的单胺氧化酶B（MAO B）不可逆的灭活剂。底物可保护酶免于灭活，但β-巯基乙醇则不能，表明这些化合物是基于机理的灭活剂。所有这三种化合物也是MAO B的底物，分配比范围为152至536。4-取代的类似物比未取代的类似物更有效的灭活剂，表明在这类灭活剂中有利于4-取代。

  DOI：

  10.1021/jm9606249

文献信息

• Thermal and Sensitiveness Determination of Cubanes: Towards Cubane‐Based Fuels for Infrared Countermeasures
  作者：Madeleine A. Dallaston、Jason S. Brusnahan、Craig Wall、Craig M. Williams

  DOI：10.1002/chem.201901086

  日期：2019.6.21

  As infrared seeking technology evolves, threats are better able to distinguish defensive infrared (IR) flares from true targets. Spectrally matched flares, which generally employ carbon‐based fuels, are better able to decoy some advanced missiles by more closely mimicking the IR emission of the target. Cubane is a high‐energy carbon‐based scaffold which may be suitable for use as a fuel in spectrally

  随着红外搜寻技术的发展，威胁可以更好地将防御性红外（IR）耀斑与真实目标区分开。通常使用碳基燃料的光谱匹配耀斑通过更接近目标的IR发射，能够更好地诱骗某些先进的导弹。Cubane是一种高能碳基支架，可能适合用作光谱匹配的火炬的燃料。在计算机上预测了一系列古巴的形成焓和应变能，并研究了它们的热稳定性和冲击稳定性。在密封细胞差示扫描量热法中发现所有样品都发生高放热分解，随后对两个培养皿进行了定量敏感性测试。尽管他们˚F的我值在二次爆炸范围是，立方烷-1,4-二羧酸（˚F的我= 70）和4- carbamoylcubane -1-羧酸（˚F的我= 90）被确定为烟火红外对抗眩光潜在有用的燃料配方。
• Cubyl amides: Novel P2X7 receptor antagonists
  作者：Hendra Gunosewoyo、Jun Liu Guo、Maxwell R. Bennett、Mark J. Coster、Michael Kassiou

  DOI：10.1016/j.bmcl.2008.05.062

  日期：2008.7

  Polycyclic amides 2 and 5-9 were successfully synthesised and their lipophilicity profiles were evaluated using reverse-phase HPLC. All synthesised compounds possessed P2X7R antagonistic properties when tested on rat spinal cord microglia cells. Extensive screening for binding to other neuroreceptor subtypes demonstrated their P2X7 selectivity.

  成功合成了多环酰胺2和5-9，并使用反相HPLC评估了它们的亲脂性。当在大鼠脊髓小胶质细胞上进行测试时，所有合成的化合物均具有P2X7R拮抗特性。与其他神经受体亚型结合的广泛筛选证明了其对P2X7的选择性。
• 4-Substituted Cubylcarbinylamines:  A New Class of Mechanism-Based Monoamine Oxidase B Inactivators
  作者：Joseph J. P. Zhou、Jianchang Li、Suhbash Upadhyaya、Philip E. Eaton、Richard B. Silverman

  DOI：10.1021/jm9606249

  日期：1997.3.1

  time-dependent, irreversible inactivators of monoamine oxidase B (MAO B). Substrate protects the enzyme from inactivation, but beta-mercaptoethanol does not, suggesting that these compounds are mechanism-based inactivators. All three compounds were also substrates for MAO B with partition ratios ranging from 152 to 536. The 4-substituted analogues were more potent inactivators than the unsubstituted analogue

  合成了苄基羰基胺（1a），（4-环丙基cubyl）羰基胺（1b）和（4-苯基cubyl）羰基胺（1c），它们是时间依赖性的单胺氧化酶B（MAO B）不可逆的灭活剂。底物可保护酶免于灭活，但β-巯基乙醇则不能，表明这些化合物是基于机理的灭活剂。所有这三种化合物也是MAO B的底物，分配比范围为152至536。4-取代的类似物比未取代的类似物更有效的灭活剂，表明在这类灭活剂中有利于4-取代。
• The role of polycyclic frameworks in modulating P2X7 receptor function
  作者：Timothy B. Callis、Tristan A. Reekie、James O'Brien-Brown、Erick C.N. Wong、Eryn L. Werry、Nabiha Elias、William T. Jorgensen、John Tsanaktsidis、Louis M. Rendina、Michael Kassiou

  DOI：10.1016/j.tet.2017.10.075

  日期：2018.3

  Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor. (C) 2017 Elsevier Ltd. All rights reserved.
• The First CNS-Active Carborane: A Novel P2X₇ Receptor Antagonist with Antidepressant Activity
  作者：Shane M. Wilkinson、Hendra Gunosewoyo、Melissa L. Barron、Aurelie Boucher、Michelle McDonnell、Peter Turner、Daniel E. Morrison、Maxwell R. Bennett、Iain S. McGregor、Louis M. Rendina、Michael Kassiou

  DOI：10.1021/cn500054n

  日期：2014.5.21

  Relative to other polycyclic frameworks (1-3), a carborane cage (4 and Cs center dot 5) exerts a significant biological effect as an inhibitor of the purinergic P2X(7) receptor (P2X(7)R) which allows one to target depression in vivo and thus demonstrate, for the first time, that a carborane has the capacity to modify CNS activity.[GRAPHICS]